A Look Inside the Design Team at FreshBooks

We’re tracking down InVision users inside the world’s most amazing companies to discover their favorite tools, inspirations, workspace must-haves and the philosophy behind what makes them so awesome.

Jeremy Bailey is the creative director at the Toronto-based FreshBooks, the #1 cloud-accounting solution designed exclusively for small business owners. With hands-on training in design since the age of 13, as well as an art school degree and years of prior agency work under his belt, Bailey leads a strong design team and also boasts a satiric creative online alter-ego, “Famous New Media Artist Jeremy Bailey.”

Here, Bailey shares his thoughts on why a small ego and empathy are designer essentials; why integrating design thinking and agile scrum development is his passion; and why you should enjoy failure (at least for a moment):

What is your role and responsibilities at FreshBooks?

As the creative director at FreshBooks, I supervise the product design and marketing design teams -- meaning I lead, inspire and motivate. It’s not just management, though, because I’m actually on a design team collaborating, driving and helping refine actual designs and processes.

How did you get your start in design, and ultimately end up at FreshBooks?

I had an unconventional start. My father ran a design agency here in Toronto and I started working with him when I was about 13. In the beginning I was just doing Photoshop jobs but grew to learn a lot of the trade hands-on. When I finished high school, I paid my way through my BA at the University of Toronto doing crazy looking interface designs – we called them Skins back then– for MP3 players. I was an Art Director for an agency called Youthography for a little while but left design to go to art school at Syracuse University where I got my MFA. When I got out of school I went back to working as an art director freelancing for some great Toronto agencies on a variety of projects.

From time to time I’d take on non-agency clients, FreshBooks was one such client and the first software company I’d worked for since my MP3 player days. At the time they had a single designer, Jeff, who did everything. My job as an Art Director was to help make sense of their brand, my approach was to act as a curator, to keep what was working and ditch the rest. I presented several failed approaches but eventually found the right focus based on the best elements customers already knew and loved. That project turned into a job offer and 4 years later I’m still here working on the same thing! Brands are defined by their customers, not their art directors. They’re not about inventing something completely new from thin air. Our customers keep growing, so we do too: we never stop listening, never stop responding.

Can you tell us about your team of designers?

We are an empathetic team of product designers and marketing designers. The six-person marketing design team is dedicated to solving marketing communications problems, we do everything in-house and don’t have an agency of record. Then we have individual product designers, who design the user experiences for our software products. They sit on interdisciplinary agile scrum teams who work one or two-week sprint cycles to develop our software products.

One challenge that can occur is that designers tend to get isolated when they are on an agile scrum team, so we offer a lot of social and education activities (we even founded an internal design school!) that bring all the designers from across the company together several times a week, including group critiques where we look at InVision prototypes and walk other team members through experiences so we can both share and keep people up to date on trends or changes. The group sessions also offer a system of checks and balances, so no one ships crazy radical explorations that impact another experience someone else is working on, or a marketing claim we might be making. It helps keep everyone aligned.

How were you doing prototyping before InVision?

Typically we’d have a screen shot; or working HTML prototype with some Javascript; or even just a paper prototype. Needless to say, the screen shots and paper prototypes didn’t work very well because we think not in terms of individual screens, but in terms of experiences. It led to a lot of “Here’s what you can expect to happen if you click on this.” And the HTML prototypes are awesome, but they drain too many resources while trying to validate, say, five radical approaches to solving a design problem. As an agile scrum company, we might only have one week to do an exploration, test it and get into the position to ship it to users so we’re in a position to iterate.

InVision is such a simple tool, it’s easy to put together a prototype we can test with users quickly so we can do that quick but fundamental, radical exploration. We had the whole team running on it in a week or two. InVision lets us spend more time designing and less time coding. But, we also find that not every problem is appropriate for InVision – we do have some experiences with richer interaction that we like to present more in-depth using an HTML prototype.

What eye-opening lesson that you've learned at FreshBooks do you wish you'd known before?

I wish I knew how generous people were with their time, even complete strangers. We have regular people, existing and new customers, who come in to test a product idea we’re working on and they might not even know who we are. They’ll help us refine and make our ideas better simply to help us. The amount of time and energy they’re willing to give us is phenomenal because it’s worth so much more than that to us.

Throwing work over the wall & pointing fingers when things go wrong creates a poor work environment.

Is there any particular issue or discussion going on in design right now that you're really interested in?

With a company like ours that’s scaling really quickly, we adopted the agile scrum as a development methodology -- not to develop faster, but to scale the organization so we could do things more efficiently and autonomously. The problem is it doesn’t really integrate design thinking, the customer focused approach we use to do our best design work. I think traditionally people think of design as this ambiguous, artsy-farsty thing that can’t be contained and doesn’t fit into agile, but the design thinking approach is actually quite rational. Design involves centering solutions around empathy for the user.

It has become my passion to figure out how to integrate both agile scrum and design thinking. At FreshBooks, we’ve struck upon some interesting ways of doing that. For example, there’s Lean UX, which helped us understand that design is not precious, it’s iterative. When you fail many times very quickly, your design only gets stronger. There’s a great example of this principle in Tom and David Kelley’s Creative Confidence where they tell the story of a pottery class, where half the class is told that they’ll be graded on the sheer quality of one pot, while the other half is graded on the number of pots they produce no matter what they look like.

The people that produced the largest number of pots had by far the highest quality and most interesting work. We’re finding that here at FreshBooks: The quality of the work gets better even as we compress the amount of time necessary to do it. That’s because we’ve changed our mindset to be about “how we might solve this problem in 10 different ways” rather than “let’s spend a month refining this design.” It’s important to spend more time trying to understand problems than defending solutions.

Have you found any good tactics to communicate with other stakeholders during that tricky feedback process?

Do you have any creative projects outside of work?

I have an artist persona who calls himself “Famous New Media Artist Jeremy Bailey.” That’s a joke, because there’s no such thing as a famous new media artist. He’s this awkward, satirically driven character who goes around as kind of a prophet who believes technology can save the world – He’s pretty excited about the future to say the least. I use this persona in comedic performances where I demonstrate augmented-reality software I’ve designed to solve the world’s problems. He’s the opposite of who I am at work, he’s a technology-first kind of person that really should take a step back and be more human.

I try to keep my work and artist personas professionally separate, but creatively speaking they inform each other continuously. Being an artist allows me to take any assumption I have, examine it critically and ask important questions that allow me to push myself further. I find it can make me a more humble and critical person and more self-reflective of the decisions I make. And my artist identity helps with my empathy at work -- for example, my character presents himself as this privileged protagonist, a white male working in technology while, as we know, there is a lot of cultural tension in the tech sector regarding the representation of women and racial minorities. It helps me be aware of these social dynamics and pushes me to be an agent for change and a supporter of equal opportunity.

Is there one piece of advice you would give designers just starting out in their careers?